Vacation Rentals By Owner In Lenox, MA

Ideally located in the heart of the Berkshires on one acre of lovely private land, this five bedroom home offers a peaceful retreat. Just a few minutes walk to the Lenox town center and 2 miles to Tanglewood. This tastefully decorated home has been recently updated. brEnjoy the best New England has to offer. brWalk to restaurants, shops, art galleries and other local attractions. Enjoy the rich culture and history of the area. Just a 5 minute drive to enjoy Edith Wharton's The Mount, Herman Melville's Arrowhead, Miraval Spa, Blantyre, Canyon Ranch. In addition a 10 minute drive to the Red Lion Inn, Norman Rockwell Museum, Berkshire Botanical Garden, Hancock Shaker Village, and Shakespeare and Company. There is nearby Highlawn Farm where you can visit the calves and purchase local products, one of our favorites. We have theaters, wineries, breweries, pumpkin patches, apple orchards, and maple syrup farms nearby as wellbrThe pastoral beauty of the surrounding area is a playground for nature lovers for all seasons. Year-round outdoor recreation includes hiking, biking, skiing, nature tours, and golfing. br

Enjoy comfortable elegance in this secluded grand home located in town

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$675.61

Ideally located just two minutes from the center of Lenox and across the street from the Miraval Resort and Spa. This expanded and restored 1860’s farmhouse offers 4 bedrooms and three full baths. The main bedroom suite in on the main level has a king bed and luxurious walk in shower. The upstairs has three bedrooms, two queen beds and one full bed. All the bedrooms have windows that let in natural light. The town just installed a sidewalk and bike path so you can walk or bike to town!brbrOur house is moving towards being as environmentally friendly as possible. We use earth friendly cleaners (including Force of Nature) and detergents, reusable products, an all organic vegetable garden (during the warm months), medicinal flowers, no chemicals used on the grounds, and composting. We are always finding new ways to lower our impact on the earth. br brCompletely renovated… big rooms, flat panel televisions, Central Air Conditioning and heat, ADT Security System, Wi-Fi and cable, hardwood floors throughout, extended eat-in-kitchen. Perfect for an extended family or two families to enjoy (there are also air mattresses ready for use). We have Medify air purifiers available that have HEPA filters, new filters are installed before each new guest (if air purifiers are requested).brbrThere are front and rear patios, gas grill, dining set, Breeo fire pit, hammock, raised herb garden, for relaxed outdoor dining and entertaining. A place to unwind and reconnect. The back yard is fenced in for dogs to safely play. brbrThe more adventurous can bike, hike and kayak on the many trails and lakes (with equipment rentals easily accessible). Tanglewood is about 10 minutes away. Take advantage of the world class facilities at the Miraval Resort and Spa including golf, fitness and recreation as well as an assortment of dining opportunities.brbrThis is a unique experience offering the privacy and relaxed atmosphere of a country home and world class amenities available at your fingertips, not to mention all the offerings of Tanglewood and the many local theater groups.

Country House

Renovated 1860's Farmhouse, across from the Miraval! Fenced in yard for dogs.

Lenox, Massachusetts, United States

4

Bed

Bath

8

Sleeps

$390.36

Step back in time within this striking 1900s Colonial-style home, a mere 7-10 minute walk from Lenox’s charming downtown. Beyond the handsome façade of this multi-story 3-bedroom abode lies a beautifully manicured garden, a spacious patio perfect for al fresco dining, and a BBQ grill waiting for your culinary exploits. On the inside, 1841 sq. feet of old-world vintage allure awaits, along with modern furnishings, lightning-fast 1 GB/s Wi-Fi, and a Spectrum HDTV with 60 channels!brThe spacebrThe SpacebrNestled on a sprawling 0.21-acre lot, our home is the perfect setting for your next laid-back getaway to Lenox – granting ample space for friends, family, and pets.brAs you roll into the private driveway, pure awe and wonder will wash over you. The beauty of the surrounding trees and the classic colonial architectural details of the house all contribute to the charm and serenity of the property.brUpon entering, you are immediately embraced by an atmosphere of unparalleled refinement and antique design elements. Each intricate detail exudes the allure of a bygone era, seamlessly interwoven with modern conveniences to provide a timeless and elegant space.brThe air of sophistication is enhanced by tasteful furnishings and welcoming decorations, along with a slew of premier amenities designed to entertain and provide seamless convenience for families and large groups:br✓ Enjoy sizzling up some scrumptious flame-grilled creations using the gas-operated BBQ grill, complete with tongs for your convenience.br✓ For classical music aficionados, Tanglewood, the famed summer home of the Boston Symphony Orchestra, is conveniently located just a 5-minute drive from our doorstep.br✓ Brace yourselves for epic board game battles after eating a delicious meal on the 6-seater dining table.br✓ Gather your loved ones for a cozy game-watching session on our couch, using our Spectrum app to stream live cable TV.brbrKitchen and Local RestaurantsbrAs you slowly roll out of bed, head over to the sleek open-plan kitchen space, where the marble-top kitchen bar beckons for mornings spent sipping coffees from our state-of-the-art Keurig machine. After your caffeine fix, cook yourself the ultimate breakfast of champions or a light brunch with our suite of high-quality cooking tools and stainless steel appliances, making your culinary endeavors an absolute breeze. Get your creative juices flowing using our:br• Full-size refrigeratorbr• Microwave, oven, and stovebr• Pots and pansbr• Oil, salt, and pepperbr• Plates, bowls, wine glasses, cups, and silverwarebr• Cooking spoon, cutting board, spoons, knives, and other utensilsbr• Samsung dishwasher for quick and easy cleanupbrbrDon’t feel like cooking Venture beyond the kitchen for a culinary adventure and savor an eclectic mix of international and local flavors within a convenient 10-15 minute walk, drive, or Uber ride away:bro American (Alta)bro French (Bistro Zinc)bro Bar/Pub (Brava, Olde Heritage Tavern, Firefly)bro Pizza (Pizzeria Boema, Betty's Pizza Shack)bro Italian (Mazzeo's Ristorante, Frankie's)bro Peruvian (Alpamayo Peruvian Cuisine)bro Asian (Burmese Bowl)bro Bakery (Patisserie Lenox)bro Breakfast (Haven, Starving Artist Cafe, Bagel&Brew, Joe's Diner)brbrbrBedrooms and BathroomsbrGet ready to sleep on cloud 9! Retreat to the privacy of your own room, a space designed with your well-being in mind. Whether you seek a quiet moment to immerse yourself in your favorite book by the soft glow of a dimly lit lamp or a peaceful night's slumber, our commitment to wellness is evident in every detail.brLay down in our ultra-comfy memory foam mattresses, swathed in only the finest linens, delicate blankets, and plump pillows carrying the promise of sweet dreams. A total of 6 guests can fall asleep comfortably here, and feature:brBedroom 1:br• Queen mattressbr• 2 nightstands with lampsbr• Chest of drawersbr• Room darkening blindsbrBedroom 2:br• 2 double mattressesbr• Chest of drawersbr• Room darkening blindsbr• MirrorbrBedroom 3:br• Queen mattressbr• Chest of drawersbr• 1 nightstand with a lampbrbrFollowing a day brimming with adventure, pamper yourself and renew your senses in the sparkling bathroom, boasting an elegant shower room and a separate freestanding bathtub. As a bonus, utilize our essential bathroom amenities to help you feel refreshed and reinvigorated:br• Hair dryerbr• Shampoo & conditionerbr• Shower gelbr• Fresh bath towelsbr• Toilet paperbrGuest accessbrThe guest will have access to the entire house.

Cozy 3BR Home w/ Yard & Patio 5 min to Tanglewood

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$439.82

A peaceful retreat with a timeless aura, this revamped 19th-century home is brimming with old-school charm–combining colonial-style architecture with a contemporary design. Nestled on a sprawling 8712 sq. ft. lot, our 4-bed home provides ample space for all. Picture yourself on the patio, relishing open-air barbecues under the warm sunshine while your pets run freely in the backyard. Ah, yes, this could be you! And extra perks await, including lightning-fast 1 GB/s Wi-Fi and a 50 HDTV!brThe spacebrStepping into this generous 2,089 sq. foot space, you'll be embraced by a historic elegance and retro allure that enriches your stay. Marvel at the rustic, gleaming hardwood flooring, the sophisticated collection of high-end furnishings, and the house's overall chic and vintage style aesthetic. Expect a bright and light-filled interior by day, inducing a calm and cozy vibe at night.brThe palpable tranquillity of our expansive estate is sure to bring you and your loved ones the relaxation you desire, allowing you to disconnect from the bustling outside world and wholly submerge into your well-deserved vacation. Feel the excitement build up as you uncover a variety of premier amenities and thrilling outdoor and historical pursuits, making our home an ideal launchpad for families & large groups seeking a laid-back getaway:br✓ Enjoy blissful mornings sipping on a perfectly brewed cup of coffee from our state-of-the-art Keurig coffee machine before taking a casual stroll through Kennedy Park (~3-minute drive).br✓ Stretch out on the comfy sectional couch and indulge in a movie marathon watching Netflix, Hulu, and Roku on the 50 HDTV.br✓ Fire up the BBQ grill and revel in the joy of alfresco dining, sharing delectable meals in the comfort of the outdoor seating on the back deck.br✓ Take advantage of being a mere 7-minute walk from Lenox's charming downtown – featuring plenty of restaurants, grocery stores, shopping centers, and boutique shops.br✓ For classical music enthusiasts, Tanglewood, the famed summer home of the Boston Symphony Orchestra, is conveniently located just a 5-minute drive from our doorstep.brbrKitchenbrRise and shine like a culinary superstar and strut your stuff in the stunning kitchen, where sleek appliances and meticulous design create the perfect recipe for unleashing your inner chef.brGet ready to sizzle and sauté in style as you bask in the luxurious touches of this bright and inviting space, complete with a marble-top island bar with 4 cushioned chairs, bountiful overhead cabinets, and a suite of high-quality cooking tools & stainless steel appliances that will bring your mouth-watering dishes to life!br• Full-size stainless steel refrigeratorbr• Microwave, oven, and stovebr• Pots and pansbr• Oil, salt, and pepperbr• Kettle, toaster, blenderbr• Dishwasher for quick and easy cleanupbr• Cooking spoon, tongs, spatula, cutting board, and other utensilsbr• Plates, bowls, wine glasses, cups, mugs, and silverwarebrbrIf you decide to eat out, savor your tastebuds in a selection of eateries and bars within a 7-10-minute walk or drive away! Tempting options await, including:bro American (Alta)bro French (Bistro Zinc)bro Bar/Pub (Brava, Olde Heritage Tavern, Firefly)bro Pizza (Pizzeria Boema, Betty'Betty's Shack)bro Italian (MazzeoMazzeo'srante, FrankiFrankie'sruvian (Alpamayo Peruvian Cuisine)bro Asian (Burmese Bowl)bro Bakery (Patisserie Lenox)bro Breakfast (Haven, Starving Artist Cafe, Bagel&Brew, Joe's Joe's)brbrBedrooms and BathroomsbrWhen you're ready to surrender to the call of sleep, our 4 bedrooms are well-prepared to drift you into dreamland. Your skin will certainly appreciate the smooth caress of the luxury linens, the extra pillows and blankets, and the comfy mattresses, ensuring a peaceful night of uninterrupted sleep. A total of 10 guests can fall asleep here comfortably, including:brBedroom 1:br• King mattressbr• 2 nightstands with lampsbr• Chest of drawersbr• Private ensuite bathroom with walk-in showerbrBedroom 2:br• Queen mattressbr• 2 nightstands with lampsbr• Chest of drawersbrBedroom 3:br• Double mattressbr• Chest of drawersbrBedroom 4:br• 2 double mattressesbr• 1 nightstandbr• Chest of drawersbr• Wardrobe with hangars and shelf spacebrAs the day draws to a close, indulge in the ultimate relaxation experience and rejuvenate your senses with a comforting soak in a bubbly bath or a rinse in a steamy shower. Each bathroom is complemented by a curated selection of essentials, ensuring you emerge refreshed and reinvigorated:br• Hair dryerbr• Shampoo & conditionerbr• Body soapbr• Fresh bath towelsbr• Toilet paperbrGuest accessbrThe guest has full access to the entire house.brOther things to notebrPlease read to learn more about our extra benefits and start planning your trip to Lenox, MA, today!br✓ Covid-19 Compliance: We prioritize your health and safety by implementing a rigorous and thorough cleaning routine – including sanitizing countertops, doorknobs, bathrooms, and other high-contact areas.br✓ Household Amenities: Our home is designed with your needs in mind, providing hangers, cleaning supplies, an iron & ironing board, and laundry facilities that include a dryer and a washer.br✓ Work from Home: Enjoy seamless connectivity with our complimentary spectrum Wi-Fi, perfect for extra-sharp 4K video quality conference calls or easily downloading large files.br✓ Pets Allowed: We welcome your four-legged furry companions, who will undoubtedly relish exploring the nearby parks with you! Please notify the host of how many you plan to bring and what size before booking the property.br✓ Self Check-in: Enjoy the ease of checking in at your leisure after 4:00 PM using the keypad. A code will be sent to you on the day of your arrival for seamless access.

Colonial House, w/Yard,7min walk to Downtown Lenox

Lenox, Massachusetts, United States

4

Bed

Bath

8

Sleeps

$1478.91

A private retreat in Berkshires set on 5 acres in prime location in Lenox - our all-season property offers secluded luxury whilst offering close proximity to Tanglewood, Ski slopes, hiking trails, Lakes, the historic town of Lenox and other Berkshire towns. Chic furnishings, eclectic artwork and modern amenities make this house the perfect spot to unwind in the Berkshires. You can rent the whole property for up to 15 people. There are two buildings on the property, the Main House sleeps 11 and the Studio sleeps 4.brbrMain House [4400sqft]: This charming 1920s log cabin has an expansive layout with a breezeway connecting a newer section. Inside you will find five well-appointed bedrooms, three beautifully renovated bathrooms and a powder room. The heart and soul of the house is an expansive living room with a brick fireplace, furnished with stylish antiques and big comfortable sofas, a TV area, and a grand piano. Step out of the living room, onto a balcony to take in the pristine views of the valley below. Right behind the living room is a study and a king bedroom with a full bath. The second floor has two spacious bedrooms (one king and three twins respectively) which share a full bath with a claw foot tub and a separate shower. At the other end of the house, you will find an inviting country kitchen that opens up to a large dining area. The farm table seats 10 comfortably, and there is an adjoining dining area for children. Above the kitchen are two queen bedrooms, a hall bathroom with shower, and a TV den. There’s high speed wifi internet throughout the house. brbrStudio [1200sqft]: Just a few steps from the main house, is our two-bedroom guest house Studio - which can only be rented by the guests in the Main House. The bright and airy guest house originally used to be a photography studio. On the ground floor there’s a new kitchen, an open plan living room and a dining area with a table that seats six. The guest house has its own wifi router for easy internet access. The ground floor bathroom also has a laundry closet. There are two bedrooms, each with a queen bed. The bedroom on the ground floor is next to the bathroom. The upstairs bedroom, located a few steps above the main living area, has lovely sky lights.brbrGazebo: This property originally used to have a clay tennis court that fell into disrepair. So we repurposed it and built a screened-in living space by the woods' edge, with a 16 seat dining table and sofas for lounging. In this substantial new space you will be able to enjoy long, leisurely meals al fresco, and then curl up for a nap while listening to birds and crickets sing. During the cold season, you can enjoy a fire in the large in-ground fire pit right outside the Gazebo.brbrNot just a conventional vacation rental, we’ve set up this property as our own retreat with a lot of thought and care. Choosing to rent a home instead of booking a hotel room allows you the space to get together with friends and family in comfort and privacy. But you shouldn't have to sacrifice the luxury you may enjoy during a hotel stay. At the end of your stay, all you need to do is pack your bags and walk out the door. We don't expect you to strip the beds or empty the fridge. The only thing we do request is to take out the garbage and the recycling to the bins in the garage. We offer a worry-free experience right up to the last moment!brbr** BEFORE YOU INQUIRE**br- We require a 3-night minimum during July and August.br- This house is pet free, there are no exceptions to the pet policy.

Luxury Berkshires Retreat in Lenox - Main House & Studio

Lenox, Massachusetts, United States

8

Bed

4

Bath

17

Sleeps

$413.01

Tucked beside a brook on a private quarry pond in Lenox adjacent to Pleasant Valley Wildlife Sanctuary, this rustic cabin - once owned by famed BSO timpanist Vic Firth - offers tranquil seclusion near Tanglewood. Warm wood interiors, a modern fully equipped kitchen, and serene woodland surroundings create a magical Berkshire retreat for nature, rest, and cultural connection.brbrPlease note that the pond and all outdoor space are open and functional from Memorial Day through Columbus Day Weekend. After that we put things like kayaks etc into storage for the winter.brbr✔ Private Pondbr✔ High-speed Wi-Fibr✔ Fully-equipped kitchenbr✔ Spacious yardbr✔ Free parkingbr✔ Outdoor grillbr✔ Air conditioningbr✔ Heatingbr✔ Pet-friendlybr✔ Pack n Play Travel Crib (Upon request)brbr➥ Right on Pleasant Valley Wildlife Sanctuary !br➥ 6 mins to Bousquet Mountain Ski Areabr➥ 6 mins to Kennedy Parkbr➥ 9 mins to Tanglewoodbr➥ 10 mins to Shakespeare & Companybr➥ 10 mins to Berkshire Museumbr➥ 12 mins to Stockbridge Bowlbr➥ 12 mins to Olivia`s Overlook at Yokun Ridge Reservebr➥ 13 mins to Hancock Shaker Villagebr➥ 16 mins to Berkshire Botanical Gardenbr➥ 18 mins to Ashuwillticook Rail Trailbr➥ 18 mins to Norman Rockwell Museumbrbr✦BEDS & BATHS✦brInside we have 3 bedrooms and 1 bathroom, all decorated tastefully to give the full nostalgic Berkshire travel experience.brbrRoom Breakdown:brMain Bedroom - 1 Queen bedbrBedroom 2 - Full Futon (tight for 2 people!)brBedroom 3 - 1 Single bed w/ trundlebrbrAll Berkshire Vacation Rental Co.™ Properties include:br - Support from full-time local team available daily from 9am to 9pmbr - Professional housekeeping & property inspection prior to guest arrivalbr - Towels, linens, and bath productsbr - At least a mornings worth of coffee to get you startedbr - Learn more @ berkshire vacation rentalbrbrCleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property.brbr• DOGS: Your dog is welcome and there is a one time fee of $100. Please include your pet in the booking so we know ahead of time. Max of 2 dogs. No other types of animals are authorized.brbrTo provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area.brbrAn L2 charger for electric vehicles is available at the property by appointment.brAs hosts, we generally like to abide by the golden rule. Treat our space well, and we`ll treat you well in return. brno smokingbrno overnight guests beyond those outlined in the bookingbrno partiesbrplease respect all quiet hoursbrPlease see guest packet for more information.

Cabin

Timpani Corners | Private Pond • AC

Lenox, Massachusetts, United States

Bed

1

Bath

5

Sleeps

$754.77

Welcome to your perfect Berkshires getaway! This beautifully appointed 3-bedroom home is located right in downtown Lenox, steps away from your favorite Lenox restaurants, shops, galleries, and everything this vibrant New England town has to offer.brbrWhether you're visiting for Naumkeag's Spring Flower Show, summer concerts at Tanglewood, fall foliage along the Mohawk trail, ski season at Bousquet Mountain, or just a relaxing escape, our home offers comfort, space, and unbeatable convenience.brbrThis beautifully appointed 3-bedroom, 3.5-bath residence blends timeless New England charm with upscale finishes in the heart of Lenox. Designed for both refined comfort and effortless gathering, the home offers an ideal layout for families or couples seeking a sophisticated Berkshires escape.brbrUpstairs, all three bedrooms create a private retreat separate from the main living areas. Two feature spa-like ensuite bathrooms with heated floors, offering warmth and comfort year-round. An additional full bathroom upstairs also includes heated floors, ensuring every guest enjoys a touch of luxury.brbrThe main level is thoughtfully designed for entertaining and relaxation. The chef’s kitchen showcases elegant quartz countertops, generous prep space, and everything needed for elevated dining at home. Tucked just off the main kitchen, the scullery offers a beautifully designed prep space that keeps the heart of the home clutter-free. Featuring additional counter space, a secondary sink, and a beverage fridge, it’s perfect for morning coffee rituals, charcuterie styling, or keeping cookware neatly tucked away while entertaining. This thoughtfully designed space allows guests to cook, gather, and host with ease — blending practicality with understated elegance. brbrCentral air and heat ensure year-round comfort, and high-speed Wi-Fi makes it easy to stay connected. For cozy evenings in, enjoy a curated selection of board games and relaxed gathering spaces designed for quality time together. A convenient half bath and practical mudroom complete the well-appointed first floor.brbrRefined finishes, spa-inspired details, and an unbeatable downtown location make this Lenox retreat the perfect blend of luxury and charm.brbrAll full bathrooms are located on the upper level, while a convenient half bath/powder room is available on the main floor for guests’ ease.brbrOther things to notebrMilage to close attractions:brTanglewood - 1.9brTom Fiorini Art Studio - 0.2brVentfort Hall Gilded Age Mansion & Museum - 0.6brKennedy Park - 0.7brShakespeare & Company - 1.0brThe Mount, Edith Wharton's Home - 2.1brMass Audubon's Pleasant Valley Wildlife Sanctuary - 2.5brBousquet Mountain Ski Area - 4.9brbrLocal Restaurants:brBistro Zinc - 0.1brBrava - 0.1brFirefly Gastropub - 0.1brHaven Cafe & Bakery - 0.1brShots Cafe - 0.1brAlta Restaurant & Wine Bar - 0.2brCello Restaurant - 0.2brFrankie's - 0.2brThe Olde Heritage Tavern - 0.2brbrLocal Grocery Stores:brLoeb's Foodtown of Lenox - 0.3brMarket 32 - 3.6brGuildo's Fresh Marketplace - 3.8brPublic Market - 5.6brbrLocal Churches:brSt. Ann's Catholic Church - 0.2brChurch on the Hill - 0.2brTrinity Episcopal - 0.4brChabad of the Berkshires - 0.5brHope Church- 1.6brUnited Methodist Church of Lenox - 3.4

Luxury 3-Bedroom Retreat in Downtown Lenox & Minutes to Tanglewood

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$398.4

Located on Housatonic Street in downtown Lenox. A beautifully renovated space fully equipped for all your needs. The kitchen counter has four seats, stainless steal appliances, and an array of cooking essentials. Provided are pots, pans, cooking utensils, glassware, dishes. The living room features a comfortable couch, two chairs and a Smart TV. Wi-Fi is available throughout the space. Central Heat and air are provided for a comfortable environment in any season. All linens and towels provided.brThe kitchen counter has four seats, stainless steal appliances, and an array of cooking essentials. Provided are pots, pans, cooking utensils, glassware, dishes. The living room features a comfortable couch, two chairs and a Smart TV. Wi-Fi is available throughout the space. Central Heat and air are provided for a comfortable environment in any season. All linens and towels provided.

Apartment

Historical Housatonic Street apartment

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$288.56

Our property is a renovated 1770s stage coach stop, with original wood floors. The upstairs of our home (with separate entrance) is our rental apartment space which is hotel style, meaning 2 big bedrooms, a big common area, a nice big bathroom, and some basic appliances (mini fridge, microwave, and coffee pot). Washing dirty dishes in our bathroom is not allowed. Paper goods will be supplied. We encourage folks to eat out, pick up food, or have food delivered. Local restaurants -Antimony, 110 Grill, Mazzeos, Jae's, Bousquet's Drifters/Lift, Alta, Brava, Heritage Tavern, Balderdash Winery, Haven, Lenox Coffee, Betty's, Zinc, Firefly, Boema Pizza, the Locker Room, Vongs, and Frankies to name just a few. There are many old Inns that also have bars and restaurants. brbrBalderdash Winery and Antimony are amazing places that have live music on the weekends!brbrThere is a community meditation field, roughly 20 acres, across the street for walking or meditating. There is a river right down the street for kayaking. There are many biking and hiking trails and outdoor spaces to enjoy only 5 minutes away. There are also beautiful places to swim nearby in the summer and ski in the winter months. Downtown Lenox and Tanglewood are less than a 10 minute drive up the street! Lenox has many great restaurants, shops, bookstore, grocery, cafes, and art galleries. brbrFor any and all animal lovers-we do have 2 adorable rescued mini donkeys that you can schedule to visit, along with some friendly chickens.brbrOur place is truly relaxing and provides you with all that you can ask for in a rental and vacation.brbr

Country House

Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$329.52

Booking for the 2022 Fall Season. For more photos and information go to our website at www.lenoxmarental.com. Enjoy the beauty of the Berkshires.brbrOn a private, dead-end road this lake front three-season cottage is the perfect place for rest and relaxation. The bright & comfortable interior will greet you upon arrival. You will quickly fall in love with this homey cottage equipped with all the conveniences you expect. The screened porch affords panoramic views of the Berkshire hills & Laurel Lake. Just outside your door you will discover your own private beach, great for sunning, swimming, boating or just exploring. Back of cottage offers a sun/partial shade lawn, 20 steps to beach. Perennial gardens border a perfect setup for outdoor entertaining. Cottage has 2 bedrooms, one with king sized bed, the other with three twin beds (that includes a bunkbed). 1.5 baths, large family room, kitchen & large screened in porch overlooking water. We are situated just 2.25 miles from the center of Lenox village and centrally located to all other Berkshire attractions

Cottage

Vacation or work away from home! Private Beach Lakefront Cottage in Lenox MA

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$894.72

Welcome to our Lenox home in the heart of the Berkshires, designed for guests who want beauty, comfort, privacy, and a sense of escape rather than a standard vacation rental experience.brbrThe house combines dramatic post-and-beam architecture with warm, comfortable interiors and changing natural light throughout the day. Oversized cathedral windows, high ceilings, and open living spaces create an atmosphere that feels both expansive and relaxing in every season.brbrThe home includes three comfortable bedrooms spread across multiple levels, offering privacy and flexibility for couples, families, or small groups traveling together.brbrInside, guests will find:br• Spacious open living and dining areasbr• Fireplacebr• Giant movie screen and projector for film nightsbr• Fast Wi-Fi suitable for streaming and remote workbr• Comfortable designer bedding and high-quality linensbr• Two spacious walk-in showers, including a spa-like second-floor bathroombr• Premium bidet/Washlet toiletbr• Premium massage chair available for guest usebr• Fully equipped kitchen for cooking and entertainingbrbrOutside:br• Saltwater pool (seasonal)br• Year-round outdoor saunabr• Outdoor dining and seating areasbr• Beautiful nearby meditation fieldsbr• Easy access to hiking trails and nature areas within minutesbrbrThe location offers convenient access to:br• Tanglewoodbr• Downtown Lenoxbr• Shakespeare & Companybr• Hiking and skiingbr• Restaurants, cafés, bookstores, and Berkshire cultural attractionsbrbrThe house is especially well suited for:br• Tanglewood weekendsbr• Couples traveling togetherbr• Quiet family gatheringsbr• Writers, artists, and remote workersbr• Fall foliage tripsbr• Cozy winter stays with movies, cooking, sauna evenings, and snow outside the windowsbrbrThis is a peaceful residential property intended for respectful guests seeking a calm Berkshire stay. No parties, events, or large gatherings.brbrWe hope guests leave feeling rested, inspired, and slightly reluctant to return to ordinary life.

Architectural Lenox Retreat with Pool and Sauna, minutes to Tanglewood

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$934.76

Step back in time into this beautifully curated victorian built in the late 1800`s right in downtown Lenox. If a simple life in The Berkshires is your dream, look no further. High ceilings, multiple fireplaces, and a large eat in kitchen will work their wonders on you. Slow down, nestle in, and relax, your one of a kind getaway to The Berkshires awaits you. Look no further, and book today before it`s too late!brbr✔ High-speed Wi-Fibr✔ TVbr✔ Fully equipped kitchenbr✔ Indoor fireplacebr✔ Washer & dryerbr✔ Free parkingbr✔ Multiple fireplacesbr✔ Secluded backyard with perennial bordersbr✔ BBQ Grillbr✔ Pack n Play Travel Crib (Upon request)brbr➥ In downtown Lenox!br➥ 3 mins to Kennedy Parkbr➥ 5 mins to Shakespeare & Companybr➥ 5 mins to Tanglewoodbr➥ 6 mins to The Mount, Edith Wharton`s Homebr➥ 7 mins to Olivia`s Overlook at Yokun Ridge Reservebr➥ 8 mins to Stockbridge Bowlbr➥ 9 mins to Bousquet Mountain Ski Areabr➥ 10 mins to October Mountain State Forestbr➥ 14 mins to Lenox Mountainbr➥ 16 mins to Hancock Shaker Villagebrbr✦BEDS & BATHS✦brInside we have 5 bedrooms and 3 bathrooms all decorated tastefully to give the full nostalgic Berkshire travel experience.brbrRoom Breakdown:brMain Bedroom - 1 King bedbrBedroom 2 - 1 Queen bedbrBedroom 3 - 1 Queen bedbrBedroom 4 - 2 Single bedsbrBedroom 5 - 1 Single bedbrbrAll Berkshire Vacation Rental Co.™ Properties include:br - Support from full-time local team available daily from 9am to 9pmbr - Professional housekeeping & property inspection prior to guest arrivalbr - Towels, linens, and bath productsbr - At least a mornings worth of coffee to get you startedbr - Learn more @berkshirevacationrentalbrbrCleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property.brbrNo pets of any kind allowed at this home. Emotional support animals are not allowed. By law service animals are allowed. If you are planning on bringing a service animal please reach out to us ahead of time so we can verify paperwork. If a pet is brought on the premises without alerting us the reservation will be cancelled.brbrCleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property.brbrTo provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area.brbrThere is space for parking two cars in the driveway. Any additional cars will need to be parked in the church lot at the bottom of St Anne`s street. brbrThere are many helpful accouterments in the house to make your stay more `home like`.brIn the kitchen, count on the usual fridge door condiments + pantry staples, sugar, flour ( if you`re into baking) coffee filters, tea bags, oils and vinegar etc. Help yourself , but please replace anything that you `use up`!brPlease ask if you need more specifics .brAs hosts, we generally like to abide by the golden rule. Treat our space well, and we`ll treat you well in return. brno smokingbrno overnight guests beyond those outlined in the bookingbrno partiesbrplease respect all quiet hoursbrPlease see guest packet for more information.

St Anne`s Manor | Walk to Downtown! • Sleeps 8

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$363.03

Just steps from our historical town, enjoy a special location in our quiet family neighborhood. Lenox offers gourmet restaurants, historical buildings and boutique shopping. With world class culture in beautiful surroundings, the Berkshires always beckon people back.brWe love our neighborhood and as full time residents are happy to offer recommendations for activities and places of interest. Our new mini-split systembroffers individualized cooling/heating inside and a covered porch in front and a patio in back provide relaxing spaces outside. brWe only have the last 2 weeks of August available. There is a 1 week minimum but time can be extended upon request. Look forward to a Beautiful Berkshire Summer!

Lovely Townhouse In Heart Of Lenox, 2 Bedroom, 2 Bath

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$657.25

Newly Renovated for 2023 Cape Cod Style ,4BR, 4BA, sleeps 10-12. New fully equipped kitchen w/ center island, barbecue, wine cooler, 2 wood burning fireplaces, large deck with 7-person hot tub and super seating for beautiful sunsets, Fabulous great room with pool table, 65' HD Smart TV and 48' HD Smart TV for your sports fans in rec room. Summer weeks include 2 rounds of golf at nearby Miraval Country club or Spa treatments for two at the Miraval Spa or trade them for show tickets, Tanglewood, Shakespeare or Jacobs Pillar performances. Both Westinghouse and Vanderbilt agreed that this was the best location in the Berkshires as they were former owners. Take a very short hike (15 mins) to the nearby Edith Wharton Estate for some great drinks, snacks, super Jazz and the beautiful gardens. Norman Rockwell, The Clark and Berkshire Museums have new exhibits. GB, Stockbridge, Lee, Pittsfield and Lenox theatres, restaurants, shopping and crafts fairs are awesome. Your table is waiting. Tanglewood picnic baskets, lawn chairs and blankets provided. Management nearby to take care of your every need. Bonus, two kayaks, 2 canoes and rowboat. Tennis on premises.

Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$554.46

Summary:brBeautifully renovated 1881 farm house minutes from down town Lenox.brbrThe Space:brQuintessential Lenox Farmhouse with 1881 charm and a shiny new finish. Lovingly renovated and restored, this house is nestled on 4.5 private acres within minutes of the town of Lenox and Tanglewood.brbrbrThe house boasts a chef's Kitchen with all new stainless steel appliances, large farmhouse porcelain sink, marble topped counters and center island. A small deck off the kitchen is the perfect spot for a sunset cocktail or morning coffee.brbrbrBeautiful Hickory barn wood floors throughout the first floor. The two bathrooms have basket weave marble floors, Victorian vanities and fixtures. Master bath has 60 double sleeper tub, walk in glass marble shower, a relaxing rain forest shower head and a bench. Spacious guest bath has claw foot tub with shower.brbrbrMaster & guest bedroom are detailed with 14' vaulted white wash tonged & grove ceilings.brbrGuest Access:brCheck in any time after 3pm.brbrThe Neighborhood:brLenox

Restored 1881 Farm House

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$598.1

5 bed rooms, 3 full baths, large kitchen with a prep pantry. Master bedroom on the 1st floor, another master on the 2nd. En-Suite in the back of the house 2nd floor with a view of October mountain, the largest state park in Massachusetts.brbr The house sits on the front of our 2-1/2 acre field, dotted with a few apple trees. br5 minutes from the bustle of downtown Lenox. 10 minutes from the great music of Tanglewood, all while in the country brbrGo for a hike in the morning, catch a play at night, or go to one of the many museums for the day and have dinner at night at one of the many 5 star restaurants in town.

The best of both worlds, Country and Culture

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$639.05

Evergreen Home Vacation Rentals invites you to experience luxury in the heart of Lenox.brbrJust 10 minutes from Bousquet Mountain, this beautifully renovated 3-bedroom, 2-bath downtown apartment blends elevated design with modern comfort. Every detail has been thoughtfully curated—from plush Parachute and Annie Selke linens to radiant heated bathroom floors.brbrEnjoy dinner downtown, then retreat to complete serenity just steps away. ✨brbrIf you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.brbrLenox is central to The Berkshires so anywhere you want to explore in the greater area like museums, hikes, skiing, theater are just a short drive awaybrbrGuests will be given a lockbox code to enter through the front door. Free off street parking is available.brbrWalk up the wide stairs into your own personal high end oasis. Quarter & Rift sawn white oak floors span The Penthouse with beautiful and comfortable furniture from Design within Reach and Rove Concepts. The Chef's kitchen features custom walnut cabinetry, Waterworks hardware, Bertazonni stove and dishwasher, Fisher & Paykel fridge and dishes and flatware from Williams Sonoma. brbrTwo Large Screen LG OLED Smart TV's, one in the great room and one in the primary suite are available. High speed Wifi will keep you connected, but if you want to unplug we have Chess, Checkers, Backgammon and other board games to enjoy. brbrThe primary suite features a king bed, walk in closet and ensuite bath with radiant floors and zero entry shower. In addition to the primary suite, The Penthouse boasts a guest bedroom with king bed and large closet. Off the great room is a second guest bedroom with two double beds allowing for accommodation of up to 6 guests. A washer and dryer is available for guest use.brbrStay cool in the summer with central AC, and warm and toasty in the colder months with the new heating system.brbrLocated above a downtown Lenox restaurant open 7 days a week, this unit has sound proofing so our guests can enjoy privacy. We do not guarantee that you won't hear noise during business hours. brbrYou may not want to leave The Penthouse, but should you venture out.... explore the many shops, studios, and restaurants in the quaint village of Lenox, MA right outside your front door. Enjoy a concert at Tanglewood, treat yourself to a spa day at Miraval, then take in a performance at Shakespeare and Company or tour Edith Warton's The Mount all under 5 minutes away. brbrThe Village of Lenox is walkable, but you will want a vehicle if you plan to explore all the Berkshires has offer.brbr⭐️ LOCATION: Lenox is centrally located in the Berkshires, with museums, hiking, skiing, theater, and more just a short drive away.brbr⭐️ PETS: Small dogs allowed with prior owner approval only. No dogs under 2 years old and no multiple pets. Please request approval before booking. A $100 pet fee applies if approved.brbr⭐️ PARKING: Free on-site parking included.brbr⭐️ BUILDING INFO: The Penthouse is located above Bistro Zinc. The kitchen is directly below the primary bedroom. While the space is sound-insulated, some noise may travel between floors. Sound machines are provided for light sleepers.br• Bistro hours: 7 days a week, 11:30am–3pm and 5pm–9pmbrbr⭐️ CHILDREN: This apartment is not suitable for small children. Please contact us prior to booking if traveling with children under 10.brbr⭐️ DAMAGE PROTECTION: Your reservation includes a $20 accidental damage insurance fee, allowing you to relax and enjoy your stay with peace of mind. If any damage occurs, please let us know so we can arrange timely replacements for the next guest.

Apartment

The Penthouse, Downtown Lenox by Evergreen Home

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$683.58

If you want to feel like you're truly away, but still have access to a great lifestyle, this is the rental for you! Stay in a charming, comfortable, renovated duplex house (side B is being offered for rent) in a beloved Summer, Fall and Winter community just steps away from tony and charming downtown Lenox. Five star restaurants, cozy cafes, bakeries, and wonderful shopping abound. Drive just a few minutes and you'll have every activity and relaxation outlet right at your fingertips. This is not to be missed! brbrTanglewood Music Center - less than 2 miles brJacobs Pillow - 20 min drive brMiraval Resort and Spa - 2 miles brCanyon Ranch - less than 2 miles brBosquet Ski Resort - 5 milesbrJiminy Peak Ski Resort - 18 miles (35 minutes)brButternut Ski Resort - 15 milesbrCatamount Ski Resort - 22 milesbrPleasant Valley Wildlife Sanctuary - less than 3 milesbrEdith Wharton's home, The Mount, less than 3 miles

Perfect location in the heart of downtown Lenox

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$416.2

Steps to Main Street | 2 Mi to Tanglewood | Private Yard w/ GrillbrbrThis Lenox vacation rental places you in the heart of the Berkshires! Steps from shops and restaurants and minutes from Tanglewood, you’ll enjoy easy access to world-class arts, culture, and outdoor adventure. The 3-bedroom, 2.5-bath home is also conveniently located within a short drive of the Appalachian Trail and ski resorts. After exploring, relax with a backyard barbecue or unwind inside with all the comforts of home.brbr-- THE PROPERTY --brbrC0514291520brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 queen bedbr- Bedroom 3: 1 full bedbrbrSTEP OUTSIDEbr- Private yard w/ gas grillbr- Front yard w/ gardenbrbrINDOOR LIVINGbr- Hardwood flooringbr- Smart TVsbr- Natural sunlightbrbrKITCHENbr- Refrigerator, stove/oven, dishwasher, microwavebr- Drip coffee maker, toaster ovenbr- Cooking basicsbrbrGENERALbr- Free WiFibr- Central heating & A/Cbr- Linens & towels, complimentary toiletriesbrbrFAQbr- Quiet hours (10:00 PM-8:00 AM)brbrACCESSIBILITYbr- 2-story home, 3 steps to enterbrbrPARKINGbr- Designated parking spaces (2 vehicles)br- Additional vehicles must be parked in public parking (not at the nearby inn)brbr-- THE LOCATION --brbr- Close to hiking trails, skiing resorts & golf coursesbr- 2 miles to The Mount, Edith Wharton's Homebr- 5 miles to Bousquet Ski Areabr- 10 miles to Fountain Pond State Parkbr- 13 miles to Appalachian Trailbr- 51 miles to Albany International Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- No pets allowed br- No events, parties, or large gatheringsbr- Additional fees and taxes may apply br- Photo ID may be required upon check-inbr- Please observe quiet hours from 10:00 PM and 8:00 AMbrbrADDITIONAL INFORMATIONbr- This 2-story home requires 3 steps to enter

Walk to Dining: Downtown Lenox Guest House!

Lenox, Massachusetts, United States